This invention relates to herbicidally active 2,6-disubstituted benzylsulfonamides and benzenesulfamates, agriculturally suitable compositions thereof and a method for their use as herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,420,325 discloses benzylsulfonylureas bearing ortho-substituents such as CO.sub.2 CH.sub.3. SO.sub.2 N(CH.sub.3).sub.2, etc.
U.S. Pat. No. 4,191,553 discloses sulfamate sulfonylureas containing ortho Cl, NO.sub.2 and OCH.sub.3 groups.
U.S. Pat. No. 4,394,153 discloses sulfamate sulfonylureas bearing ortho alkyl sulfonate groups.
Japanese Patent Application No. 112,916, published Jan. 29, 1983, discloses sulfamate sulfonylureas of the general formula: ##STR1## wherein X may be H, halogen, lower alkyl, NO.sub.2, CO.sub.2 H, lower alkoxycarbonyl; and
Y may be H, halogen or CF.sub.3. PA1 R.sub.1 is CO.sub.2 R.sub.4, SO.sub.2 NR.sub.5 R.sub.6, SO.sub.2 N(OCH.sub.3)CH.sub.3, SR.sub.7, SO.sub.2 R.sub.7, NO.sub.2, OCF.sub.2 H, OSO.sub.2 R.sub.8 or C(O)NR.sub.11 R.sub.12 ; PA1 R.sub.2 is H, CO.sub.2 R.sub.4, SO.sub.2 NR.sub.5 R.sub.6, SO.sub.2 N(OCH.sub.3)CH.sub.3, SR.sub.7, SO.sub.2 R.sub.7, NO.sub.2, OCF.sub.2 H or OSO.sub.2 R.sub.8 ; PA1 R.sub.3 is H, CH.sub.3, OCH.sub.3, Cl or F; PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.5 and R.sub.6 are independently C.sub.1 14 C.sub.2 alkyl; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl, CF.sub.2 H or CF.sub.3 ; PA1 R.sub.8 is C.sub.1 -C.sub.3 alkyl, CF.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.9 is CO.sub.2 R.sub.4, SO.sub.2 NR.sub.5 R.sub.6, SO.sub.2 N(OCH.sub.3)CH.sub.3, SR.sub.7, SO.sub.2 R.sub.7, OCF.sub.2 H or OSO.sub.2 R.sub.8 ; PA1 R.sub.10 is CO.sub.2 R.sub.4, SO.sub.2 NR.sub.5 R.sub.6, SO.sub.2 N(OCH.sub.3)CH.sub.3, SR.sub.7, SO.sub.2 R.sub.7, OCF.sub.2 H or OSO.sub.2 R.sub.8 ; PA1 R.sub.11 is H, C.sub.1 -C.sub.2 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.12 is H or C.sub.1 -C.sub.2 alkyl; or PA1 R.sub.11 and R.sub.12 may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 A is ##STR4## X is CH.sub.3, OCH.sub.3, OCF.sub.2 H, F, Cl or Br; Y is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCF.sub.2 H, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, SCH.sub.3 or OCH.sub.2 CF.sub.3 ; PA1 Z is CH or N; PA1 X.sub.1 is CH.sub.2 or O; PA1 Y.sub.1 is CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 Y.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA1 Y.sub.3 is H or CH.sub.3 ; PA1 R.sub.1 is other than C(O)NR.sub.11 R.sub.12. PA1 R.sub.1 is other than C(O)NR.sub.11 R.sub.12. PA1 R.sub.1 is other than C(O)NR.sub.11 R.sub.12. PA1 R.sub.1, R.sub.2 and R.sub.3 are as previously defined. PA1 R.sub.1 or R.sub.2 is SR.sub.7.
DE No. 3,151,450 discloses herbicidal sulfamates of formula ##STR2## where R.sub.1 and R.sub.2 are independently H, halo, alkoxycarbonyl, alkyl, alkoxy, alkylthio, CF.sub.3, CN, cycloalkyl, nitro or dialkylamino.